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Further Investigation of the Nature of the C‐Li Bond. Structures of a Phenylthiomethyllithium Complex and ofa Methylthiomethyllithium Complex
Author(s) -
Amsturz René,
Laube Thomas,
Schweizer W. Bernd,
Seebach Dieter,
Dunitz Jack D.
Publication year - 1984
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19840670129
Subject(s) - chemistry , tetramethylethylenediamine , ring (chemistry) , crystallography , atom (system on chip) , thioanisole , crystal structure , unit (ring theory) , stereochemistry , medicinal chemistry , biochemistry , mathematics education , mathematics , organic chemistry , computer science , embedded system , catalysis
Phenylthiomethyllithium/ N , N , N ′, N ′‐tetramethylethylenediamine (TMEDA) (1:1) is shown by X‐ray analysis to be dimeric in the crystalline state. The structural unit contains a six‐membered ring in which each Li is bonded to the terminal C atom of one thioanisole and to the S atom of the other, as well as to the two N atoms of a TMEDA. Methylthiomethyllithium/TMEDA (1:1) is also dimeric, but the structural unit contains a four‐membered ring in which each Li is bonded to two C atoms and to the two TMEDA N atoms. An error has been detected in an earlier published electron‐density difference map for 2‐lithio‐2‐phenyl‐1, 3‐dithiane/TMEDA/THF (1:1:1). The conclusion drawn then that this complex exists as a tight ion‐pair in the crystal is now retracted.